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【结 构 式】

【分子编号】37317

【品名】(2R)-3-[[(4-methoxyphenyl)(diphenyl)methyl]sulfanyl]-2-[(2-naphthylsulfonyl)amino]propionic acid

【CA登记号】

【 分 子 式 】C33H29NO5S2

【 分 子 量 】583.729

【元素组成】C 67.9% H 5.01% N 2.4% O 13.7% S 10.99%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Condensation of S-(4-monomethoxytrityl)-L-cysteine (I) with 2-naphthalenesulfonyl chloride (II) under Schotten-Baumann conditions afforded sulfonamide (III). Cleavage of the trityl group of (III) by treatment with trifluoroacetic acid and triisopropylsilane gave thiol (IV), which was protected as the thiopyridyl derivative (V) using dithiodipyridine. Coupling of (V) with 4-amidinophenylalanyl piperidine (VI) by means of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide - HCl (EDC), 1-hydroxybenzotriazole (HOBt) and N-ethylmorpholine (NEM) furnished dipeptide (VII). The thiopyridyl group of (VII) was then deprotected by treatment with tributyl phosphine to afford thiol (VIII).

1 Buijsman, R.C.; van Boeckel, C.A.A.; van der Marel, G.A.; Basten, J.E.M.; van Dinther, T.G.; van Boom, J.H.; Design and synthesis of a novel synthetic NAPAP-pentasaccharide conjugate displaying a dual antithrombotic action. Bioorg Med Chem Lett 1999, 9, 14, 2013.
2 Van Boeckel, C.A.A.; Basten, J.E.M.; Dreef-Tromp, C.M.; Buijsman, R.C. (Akzo Nobel N.V.; Universiteit Leiden); Antithrombotic cpds.. WO 9965934 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 22457 2,2'-Dithiodipyridine; 2-(2-pyridinyldisulfanyl)pyridine; 2,2'-Dipyridinyl disulfide 2127-03-9 C10H8N2S2 详情 详情
(I) 37316 (2R)-2-amino-3-[[(4-methoxyphenyl)(diphenyl)methyl]sulfanyl]propionic acid C23H23NO3S 详情 详情
(II) 27989 2-naphthalenesulfonyl chloride 93-11-8 C10H7ClO2S 详情 详情
(III) 37317 (2R)-3-[[(4-methoxyphenyl)(diphenyl)methyl]sulfanyl]-2-[(2-naphthylsulfonyl)amino]propionic acid C33H29NO5S2 详情 详情
(IV) 37318 (2R)-2-[(2-naphthylsulfonyl)amino]-3-sulfanylpropionic acid C13H13NO4S2 详情 详情
(V) 37319 (2R)-2-[(2-naphthylsulfonyl)amino]-3-(2-pyridinyldisulfanyl)propionic acid C18H16N2O4S3 详情 详情
(VI) 37320 4-[2-amino-3-oxo-3-(1-piperidinyl)propyl]benzenecarboximidamide C15H22N4O 详情 详情
(VII) 37321 (2R)-N-[1-[4-[amino(imino)methyl]benzyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[(2-naphthylsulfonyl)amino]-3-(2-pyridinyldisulfanyl)propanamide C33H36N6O4S3 详情 详情
(VIII) 37322 (2R)-N-[1-[4-[amino(imino)methyl]benzyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[(2-naphthylsulfonyl)amino]-3-sulfanylpropanamide C28H33N5O4S2 详情 详情
Extended Information